Page 9 of 14
The Journal of Organic Chemistry
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2H), 3.66 (s, 2H), 2.53 (s, 3H); 13C NMR (CDCl3, 150 MHz) δ (ppm) 153.1, 138.1, 137.4, 135.0, 134.1,
129.3, 129.2, 128.9, 128.3, 128.2, 128.1, 128.0, 127.1, 126.2, 123.4, 58.4, 39.0, 31.1. HRMS (ESIꢀTOF)
m/z: [M + H]+ Calcd for C24H23ClN3 388.1575; Found 388.1596.
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1-(4-Chlorophenyl)-5-(4-methylbenzyl)-N,N-dipropyl-1H-imidazol-2-amine (7f). Light yellow oil (yield
0.619 g, 81%); 1H NMR (CDCl3, 600 MHz) δ (ppm) 7.35 (d, J = 8.4 Hz, 2H), 7.02ꢀ6.98 (m, 4H), 6.84 (d,
J = 7.2 Hz, 2H), 6.64 (s, 1H), 3.57 (s, 2H), 2.86 (t, J = 7.2 Hz, 4H), 2.30 (s, 3H), 1.38ꢀ1.34 (m, 4H), 0.71
(t, J = 7.2 Hz, 6H); 13C NMR (CDCl3, 150 MHz) δ (ppm) 151.8, 135.8, 134.9, 134.7, 134.2, 129.3, 129.2,
128.9, 128.8, 128.7, 128.2, 53.7, 30.7, 20.9, 20.8, 11.3. HRMS (ESIꢀTOF) m/z: [M + Na]+ Calcd for
C23H28ClN3Na 404.1864; Found 404.1845.
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N-Benzyl-1-(4-fluorophenyl)-N-methyl-5-(4-methylbenzyl)-1H-imidazol-2-amine (7g). Light yellow oil
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(yield 0.632 g, 82%); H NMR (CDCl3, 600 MHz) δ (ppm) 7.21 (d, J = 7.8 Hz, 3H), 7.04ꢀ6.97 (m, 8H),
6.83 (d, J = 7.2 Hz, 2H), 6.66 (s, 1H), 4.05 (s, 2H,), 3.59 (s, 2H), 2.58 (s, 3H), 2.29 (s, 3H); 13C NMR
(CDCl3, 150 MHz) δ (ppm) 162.9, 161.3, 152.5, 137.2, 135.8, 134.7, 132.0, 129.8, 129.7, 129.4, 128.9,
128.2, 128.0, 127.2, 121.9, 116.2, 116.1, 58.2, 39.0, 30.7, 20.9. HRMS (ESIꢀTOF) m/z: [M + H]+ Calcd
for C25H25FN3 386.2027; Found 386.2031.
5-(4-Methylbenzyl)-2-(pyrrolidin-1-yl)-1-(p-tolyl)-1H-imidazole (7h). Light yellow oil (yield 0.570 g,
86%); 1H NMR (CDCl3, 600 MHz) δ (ppm) 7.13 (d, J = 7.2 Hz, 2H), 6.99 (t, J = 7.8 Hz, 4H), 6.88 (d, J =
7.8 Hz, 2H), 6.49 (s, 1H), 3.54 (s, 2H), 3.03 (t, J = 7.2 Hz, 4H), 2.38 (s, 3H), 2.29 (s, 3H), 1.73ꢀ1.71 (m,
4H); 13C NMR (CDCl3, 150 MHz) δ (ppm) 152.1, 137.9, 135.7, 135.4, 134.4, 129.5, 128.7, 128.4, 128.3,
128.2, 122.4, 49.5, 30.7, 25.1, 21.1, 20.9. HRMS (ESIꢀTOF) m/z: [M + H]+ Calcd for C22H26N3 332.2121;
Found 332.2119.
5-(4-Chlorobenzyl)-1-phenyl-N,N-dipropyl-1H-imidazol-2-amine (7i). Light yellow oil (yield 0.655 g,
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89%); H NMR (CDCl3, 600 MHz) δ (ppm) 7.36ꢀ7.02 (m, 7H), 6.86 (d, J = 8.4 Hz, 2H), 6.63 (s, 1H),
3.61 (s, 2H), 2.83 (t, J = 7.2 Hz, 4H), 1.35ꢀ1.30 (m, 4H), 0.68 (t, J = 7.2 Hz, 6H); 13C NMR (CDCl3, 150
MHz) δ (ppm) 152.7, 137.0, 136.7, 131.7, 129.7, 128.9, 128.1, 128.0, 127.9, 127.8, 123.3, 53.7, 30.6, 20.8,
11.2. HRMS (ESIꢀTOF) m/z: [M + H]+ Calcd for C22H27ClN3 368.1888; Found 368.1873.
N,5-Dibenzyl-1-(2-chlorophenyl)-1H-imidazol-2-amine (7j). White solid (yield 0.538 g, 72%), mp 90ꢀ91
°C; 1H NMR (CDCl3, 600 MHz) δ (ppm) 7.44 (d, J = 7.8 Hz, 1H), 7.34ꢀ7.11 (m, 10H), 7.00 (d, J = 7.8 Hz,
1H), 6.90 (d, J = 6.6 Hz, 2H), 6.64 (s, 1H), 4.57ꢀ4.48 (m, 2H), 3.69 (d, J = 16.2 Hz, 1H), 3.56ꢀ3.51 (m,
2H); 13C NMR (CDCl3, 150 MHz) δ (ppm) 149.4, 139.2, 138.2, 133.7, 132.5, 130.8, 130.6, 130.5, 128.5,
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